Synthesis of 5-fluoro-7, 12-dimethylbenz [a] anthracene-3, 4-dione: nucleophilic displacement of fluorine in polyaromatic hydrocarbons

YM Sheikh, N Ekwuribe, B Dhawan…

Index: Sheikh, Younus M.; Ekwuribe, Nnochiri; Dhawan, Balram; Witiak, Donald T. Journal of Organic Chemistry, 1982 , vol. 47, # 22 p. 4341 - 4344

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Citation Number: 3

Abstract

The synthesis of 5-fluoro-7, 12-dimethylbenz [a] anthracene-3, 4-dione (24) from 3-acetyl-1- fluoro-7-methoxy-naphthalene (12) via 5-fluoro-3-methoxy-7, 12-dimethylbenz [a] anthracene (20) is described. Unexpectedly reaction of 20 with ethylthio anion and BBr3/CH2C12 yielded 5-(ethylthio)-3-hydroxy-7, 12-dimethylbenz [a] anthracene and the 5- bromo-% hydroxy compound. To our knowledge this novel displacement has no ...